A native of Southern California, McCrary began his acting career when he was eight years old and, at age 13, he was playing the role of Eddie Winslow on the sitcom Family Matters. By age 21, McCrary had shared the screen with stars such as Robert De Niro, Gene Hackman, and Willem Dafoe.

His television credits include Committed, Eve, Girlfriends, Moesha, Don King: Only in America, the mini-series Kingpin, and the made-for-television movie Something to Sing About. McCrary has also been in films such as Mississippi Burning, Vampires: Los Muertos, Transformers, Big Shots, Steppin: The Movie, SAW VI, and Hostage.